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Renner, MK, Jensen PR, Fenical W.  2000.  Mangicols: Structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the genus Fusarium. Journal of Organic Chemistry. 65:4843-4852.   10.1021/jo000081h   AbstractWebsite

A marine fungal isolate, tentatively identified as Fusarium heterosporum, has been found to produce a series of structurally novel sesterterpene polyols, the mangicols A-G (4-10). The structures of the new compounds, including the stereochemistry of mangicol A, were assigned by interpretation of spectral data derived from both natural products and synthetic derivatives. The mangicols, which possess unprecedented spirotricyclic skeletal components, show only weak to modest cytotoxicities toward a variety of cancer cell lines in in vitro testing. Mangicols A and B, however, showed significant antiinflammatory activity in the PMA (phorbol myristate acetate)-induced mouse ear edema model. A biosynthetic pathway for the neomangicol and mangicol carbon skeletons is proposed on the basis of the incorporation of appropriate radiolabeled precursors.

Renner, MK, Jensen PR, Fenical W.  1998.  Neomangicols: Structures and absolute stereochemistries of unprecedented halogenated sesterterpenes from a marine fungus of the genus Fusarium. Journal of Organic Chemistry. 63:8346-8354.   10.1021/jo981226b   AbstractWebsite

Three novel sesterterpenes, neomangicols A-C (1-3) were isolated from the mycelial extract of a marine fungus belonging within the genus Fusarium. The carbon skeleton of the neomangicols is undescribed and constitutes a new class of C-25 rearranged sesterterpenes. The structures of the new metabolites were determined by 1D and 2D NMR methods, and the absolute configuration of 3 was determined by Mosher ester analysis of a diacetonide derivative. The configurations of the three stereocenters in the side-chain were assigned on the basis of molecular modeling and NOESY NMR correlations observed for several diacetonide derivatives of 3. Neomangicols A and B are cytotoxic against HCT-116 human colon carcinoma in in vitro evaluation, while neomangicol B inhibits the growth of the Gram-positive bacterium Bacillus subtilus with a potency similar to that of the antibiotic gentamycin.

Renner, MK, Shen YC, Cheng XC, Jensen PR, Frankmoelle W, Kauffman CA, Fenical W, Lobkovsky E, Clardy J.  1999.  Cyclomarins A-C, new antiinflammatory cyclic peptides produced by a marine bacterium (Streptomyces sp.). Journal of the American Chemical Society. 121:11273-11276.   10.1021/ja992482o   AbstractWebsite

Three new cyclic heptapeptides, cyclomarins A-C (1-3), were isolated from extracts of a cultured marine bacterium collected in the vicinity of San Diego, CA. The major metabolite, cyclomarin A (1), contains three common and four unusual (or unique) amino acids. The structures of the new metabolites were determined using 1D and 2D NMR methods, and the stereochemistry was determined from an X-ray crystal structure of the diacetate derivative of 1. Cyclomarin A (1) displays significant antiinflammatory activity in both in vivo and in vitro assays.

Rowley, DC, Kelly S, Kauffman CA, Jensen PR, Fenical W.  2003.  Halovirs A-E, new antiviral agents from a marine-derived fungus of the genus Scytalidium. Bioorganic & Medicinal Chemistry. 11:4263-4274.   10.1016/s0968-0896(03)00395-x   AbstractWebsite

Marine micro-organisms represent an under explored resource for the discovery of novel antiviral agents. Here, we describe a series of peptides designated halovirs A-E (1 5) that are produced during the saline fermentation of a marine-derived fungus of the genus Scytalidium. These lipophilic, linear peptides are potent in vitro inhibitors of the herpes simplex viruses I and 2. Evidence is presented that the halovirs directly inactivate herpes viruses, a mechanism of action that could be applicable in the prevention of HSV transmission. The total structures of these new compounds were established by a combination of spectral and chemical techniques. Salient structural features of the halovir hexapeptides include a nitrogen terminus acylated by myristic (C14) or lauric (C12) acid, an unusual Aib-Hyp dipeptide segment, and a carboxyl terminus reduced to a primary alcohol. A qualitative analysis of the secondary structures of these molecules using variable temperature NMR experiments and NOE analyses is also reported. Published by Elsevier Ltd.

Rowley, DC, Kelly S, Jensen P, Fenical W.  2004.  Synthesis and structure-activity relationships of the halovirs, antiviral natural products from a marine-derived fungus. Bioorganic & Medicinal Chemistry. 12:4929-4936.   10.1016/j.bmc.2004.06.044   AbstractWebsite

The halovirs are linear, lipophilic peptides produced by a marine-derived fungus of the genus Seytalidium. We recently reported that these molecules possess potent in vitro activity against the herpes simplex viruses I and 2. Here we present structure-activity relationships defining key structural elements for optimal viral inhibition. Results demonstrate that an N-alpha-acyl chain of at least 14 carbons and an Aib-Pro dipeptide are critical for maintaining the antiviral activity. (C) 2004 Elsevier Ltd. All rights reserved.

Ruckert, C, Leipoldt F, Zeyhle P, Fenical W, Jensen PR, Kalinowski J, Heide L, Kaysser L.  2015.  Complete genome sequence of Streptomyces sp CNQ-509, a prolific producer of meroterpenoid chemistry. Journal of Biotechnology. 216:140-141.   10.1016/j.jbiotec.2015.08.009   AbstractWebsite

Streptomyces sp. CNQ-509 is a marine actinomycete belonging to the MAR4 streptomycete lineage. MAR4 strains have been linked to the production of diverse and otherwise rare meroterpenoid compounds. The genome sequence of Streptomyces sp. CNQ-509 was found to contain 29 putative gene clusters for the biosynthesis of secondary metabolites, some of them potentially involved in the formation of meroterpenoid molecules. (C) 2015 Elsevier B.V. All rights reserved.

Rychnovsky, SD, Skalitzky DJ, Pathirana C, Jensen PR, Fenical W.  1992.  Stereochemistry of the Macrolactins. Journal of the American Chemical Society. 114:671-677.   10.1021/ja00028a039   AbstractWebsite

The macrolactins are a group of six 24-membered ring lactones isolated from a taxonomically-undefinable deep sea bacterium. Macrolactin A, the parent aglycone, shows a number of interesting biological activities, including the protection of T-lymphoblast cells against human HIV viral replication. Herein we report the stereochemistries of macrolactin B and macrolactin F, which were determined by a combination of C-13-acetonide analysis using isotopically enriched acetone, oxidative degradation, and chemical correlation. Macrolactins B and F were found to have the same stereochemistry at each of the common stereogenic centers, and so we expect that macrolactin A, the aglycone of macrolactin B, has the stereochemistry 7S,13S,15R,23R.